Scotland in 1585
In May 1585, Elizabeth, alarmed at the progress of the Catholic League in France and the success of Alexander Farnese, Duke of Parma in the Netherlands, selected Wotton as envoy to Scotland to persuade James VI to enter into an offensive and defensive alliance and to take the Dutch under his protection. He was also to suggest James's marriage to Anne of Denmark or Arabella Stewart, but it was not until six years later that the former scheme was adopted. Wotton received his instructions from his friend Sir Philip Sidney on 15 May, was at Berwick on the 26th, and was received by James VI at Edinburgh on the 30 May 1586. The Scottish court was dominated by James Stewart, Earl of Arran. Wotton's mission was to undermine him, as well as negotiate an Anglo-Scottish treaty.
There was plague in Edinburgh, and Wotton joined the king at Falkland Palace in the Fife countryside. Wotton brought James VI an offer of a regular payment or subsidy of 20,000 crowns, but was quickly advised by Francis Walsingham that the sum could only be £3,000 sterling. Walsingham gave him instructions and Wotton was to tell James that Elizabeth I was in favour of him marrying a Danish princess. Wotton discussed the proposals with James privately in a gallery at Falkland.
Assisted by Robert Zinzan alias Alexander, Wotton brought a gift of horses and hunting dogs which delighted the young king. James asked Zinzan to stay at Falkland for a while, but he returned to London with a report of Wotton's progress. A Danish embassy arrived in Scotland, and Walsingham wrote that it would good for Wotton to meet with them. Wotton's dealings with the Danish diplomats were described by James Melville of Halhill.
At first Wotton's success appeared complete; James agreed to the proposal for a league, and on 28 June 1585 the Parliament of Scotland approved. In the same month, however, the exiled Scots in England made a raid into Scotland, supported by an English force, and, though Elizabeth ordered the arrest of the offenders, James, with some reason, suspected the complicity of the English government and feared a repetition of the attempts to restore the exiled lords by force. Moreover, the Earl of Arran's influence over the king was still supreme, and Arran was strenuously supported by the French party.
Wotton found an ally in the Master of Gray, who proposed assassinating Arran. King James was disappointed when another gift of hunting hounds from England was late or delayed, and complications arose with the murder of Lord Russell (son of Francis Russell, 2nd Earl of Bedford) on 27 July 1585 at a day of truce at the border. Thomas Kerr of Fernihirst was involved in the incident, and charged to produce the offender. The Earl of Arran was implicated, and Elizabeth now sought to use the circumstance to ruin him. Wotton demanded his arrest and removal to England for trial, but James merely confined him at St Andrews Castle and then Kinneil House, whence he was soon released and resumed his ascendancy over James. Wotton's position was now precarious, and in August, Arran's ally, William Stewart of Houston openly insulted him in the king's presence. Elizabeth, however, hesitated to risk an open breach with James by effectively supporting her ambassador.
Henry III of France sent Michel Castelnau de Mauvissière to Scotland to reinforce French influence at Edinburgh, strengthening James in his refusal to give up Arran, and making Wotton's success hopeless. Wotton now advocated an incursion by the exiled lords, supported by an English force, and the seizure of James and Arran as the only means of restoring English prestige. But, aware of the danger to himself in such an event, he begged for his recall. This was granted on 11 October. Before Walsingham's letters could arrive Wotton slipped away in the night from the Scottish court at Stirling Castle and crossed the border, and on the 12 October he was at Berwick-upon-Tweed.